Dimethylformamide → N-(4-fluorophenyl)-N-(6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-yl)cyclopropane-1,1-dicarboxamide

HRID 2241209Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[N:23]=[CH:22][C:21](N)=[CH:20][CH:19]=4)=[C:11]3[C:10]([CH3:25])=[N:9]2)=[CH:5][CH:4]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]2([C:41](F)=[O:42])[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1.C[N:45](C=O)C.CCN(C(C)C)C(C)C>O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]([C:21]2[CH:22]=[N:23][C:18]([O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]4[N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=5)[N:9]=[C:10]([CH3:25])[C:11]=34)=[CH:19][CH:20]=2)[C:36]([C:38]2([C:41]([NH2:45])=[O:42])[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 100 mL round-bottomed flask was charged with 6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-amine (0.500 g, 1.38 mmol), 1-((4-fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride (0.545 g, 2.42 mmol; prepared as in Example 6, Step A), and DMF (10 mL). DIEA (0.723 mL, 4.15 mmol) was added under nitrogen and the reaction mixture was heated at 50° C. for 18 hours. The reaction mixture was cooled to room temperature, diluted with water (100 mL), and extracted with EtOAc (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to provide the crude product (1.55 g, 59%). LRMS (esi+) 567 (M+H).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc (50 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f55968349cd04124a965ba67263ed607
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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